Problems and exercisesThe Wittig reaction and related processes

Propose a synthesis of (Z)-hex-3-en-1-ol, the “leaf alcohol” responsible for the smell of freshly cut grass, by a Wittig reaction. What precautions would you take to make the alkene Z?

What product is obtained by treating cyclohexanecarbaldehyde with (a) Ph₃P=CHCO₂Et in CH₂Cl₂ and (b) (CF₃CH₂O)₂P(O)CH₂CO₂Me with KHMDS and 18-crown-6 at −78 °C? Why is the stabilized ylide not useful for olefinating cyclohexanone?